Core-Substituted Naphthalenediimides: LUMO Levels Revisited, in Comparison with Preylenediimides with Sulfur Redox Switches in the Core.

ABSTRACT: Core-substituted naphthalenediimides (NDIs) attract increasing attention to bind, transport, and transform electrons, anions, anionic intermediates, and anionic transition states, and to shine as most colorful rainbow fluorophores. The energy level of their lowest unoccupied molecular orbital (LUMO) is decisive for many of these applications. Here, differential pulse voltammetry (DPV) measurements for a consistent series of NDIs are reported to extract exact LUMO levels under identical conditions. The influence of primary and secondary substituents in the core and on the primary imides is compared with general trends for the reliable prediction of LUMO levels in functional systems. Emphasis is on sulfur redox switches in the NDI core because of their frequent use as isostructural probes fo

SUBMITTER: Miros FN 

PROVIDER: S-EPMC4984407 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature